Author: Jessica.F

1,3-Dipolar cycloaddition reaction on carbohydrate template: Stereoselective synthesis of glyco-spiro-heterocycles was written by Prasanna, R.;Purushothaman, S.;Raghunathan, R.. And the article was included in Tetrahedron in 2020.Synthetic Route of C4H7NO2S This article mentions the following:

A simple and an efficient stereoselective synthesis of glyco-spiro-heterocycles has been accomplished via 1, 3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylide generated by decarboxylative condensation of N-alkylated α-amino acids with various diketones was trapped by sugar derived dipolarophiles to give glyco-spiro-heterocycles in good yield (72-94%). All the cycloadducts were well characterized by FT IR, NMR, HRMS and HPLC. The structures were established by 2D NMR. The regio- and stereochem. outcome of some of the cycloadducts were confirmed by a single crystal X-ray anal. Effect of various solvents on 1, 3 DC reaction was also studied. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Synthetic Route of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Synthetic Route of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

A Convenient Synthesis of Thiazolidin-2-ones from Thiazolidine-2-thiones: Antibiotic Activity and Revisiting the Mechanism was written by Deng, Xiao-Bing;Chen, Ning;Wang, Zhi-Xin;Li, Xin-Yao;Hu, Hong-Yan;Xu, Jia-Xi. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.Computed Properties of C6H11NS2 This article mentions the following:

Various substituted thiazolidin-2-ones were synthesized from the corresponding thiazolidine-2-thiones with bromoethanol in ethanol with sodium ethoxide as a base. The optimal reaction conditions and mechanism were reinvestigated in detail. The bioassay indicated that (S)-4-iso-butylthiazolidin-2-one and (S)-4-benzylthiazolidin-2-one show certain inhibitive activities against Candida albicans and Escherichia coli. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Computed Properties of C6H11NS2).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine is an important scaffold and has a wide range of promising biological activities. Thiazolidine derivatives have reported anti-inflammatory and anti-nociceptive activity. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.Computed Properties of C6H11NS2

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Crystal structures of two triazola-dioxola-benzenacyclononaphanes was written by Viswanathan, Vijayan;Rao, Naga Siva;Raghunathan, Raghavachary;Velmurugan, Devadasan. And the article was included in Acta Crystallographica, Section E: Crystallographic Communications in 2015.Reference of 444-27-9 This article mentions the following:

In the title compounds, C₂₅H₂₉BrN₅O₇, (I) [systematic name: (Z)-1⁵-bromo-3²,3²-dimethyl-2¹-nitro-2²,2³,2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-decahydro-2¹ H,6¹ H-4,9-dioxa-2(3,2)-pyrrolizina-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], and C₂₄H₂₉N₅O₇S, (II) [systematic name: (Z)-3²,3²-dimethyl-2⁷-nitro-2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-octahydro-2¹ H,2³ H,6¹ H-4,9-dioxa-2(5,6)-pyrrolo[1,2-c]thiazola-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], the triazole rings adopt almost planar conformations. In (I), the fused pyrrolidine rings adopt envelope conformations with the C atoms opposite the fused N-C bond as the flap in each ring, and their mean planes are inclined to one another by 52.8 (3)°. In (II), the pyrrolidine and thiazole rings are both twisted on the fused N-C bond, and their mean planes are inclined to one another by 70.8 (2)°. In both (I) and (II), the furan ring adopts an envelope conformation with the adjacent C atom of the macrocycle as the flap. In the crystal of (I), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming sheets parallel to (10-1), while in (II), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming helical chains propagating along [010], which are linked via C-H···S hydrogen bonds, forming slabs parallel to (001). In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Reference of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine derivatives have been found to exhibit very prominent anti-inflammatory and anti-nociceptive activity. Open-chain compounds are obtained when thiazolidines are treated with tris(trimethylsilyl)silane in a reaction in which the thiazolidine derivatives act as a source of α-aminoalkyl radicals.Reference of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Stereoselective syntheses of (+)-isoretronecanol and (+)-5-epi-tashiromine via addition of chiral titanium(IV) enolates to cyclic N-acyliminium ions was written by Pereira, Elaine;de Fatima Alves, Conceicao;Bockelmann, Maria Alice;Pilli, Ronaldo A.. And the article was included in Quimica Nova in 2008.Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione This article mentions the following:

The stereoselective addition of the titanium (IV) enolates derived from (S)-4-isopropyl-N-4-chlorobutyryl-1,3-thiazolidine-2-thione and from (S)-4-isopropyl-N-4-chloropentanoyl-1,3-thiazolidine-2-thione to N-Boc-2-methoxypyrrolidine afforded the addition products (+)-I [R = (CH₂)₂Cl, (CH₂)₃Cl, resp.] in 84% yield in both cases, as 8.6:1 and 10:1 diastereoisomeric mixtures, resp. A three-step sequence allowed to convert these adducts to (+)-isoretronecanol and (+)-5-epi-tashiromine II [X = CH₂, (CH₂)₂, resp.] in 43% and 49% overall yield, resp. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. The thiazolidine ring is a cyclic N,S acetal, and most syntheses of perhydrothiazolo [3,2-a]pyridines construct the five-membered ring by condensation of aldehydes or ketones either as such or masked. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Thioproline formation as a driver of formaldehyde toxicity in Escherichia coli was written by Patterson, Jenelle A.;He, Hai;Folz, Jacob S.;Li, Qiang;Wilson, Mark A.;Fiehn, Oliver;Bruner, Steven D.;Bar-Even, Arren;Hanson, Andrew D.. And the article was included in Biochemical Journal in 2020.Synthetic Route of C4H7NO2S This article mentions the following:

Formaldehyde (HCHO) is a reactive carbonyl compound that formylates and cross-links proteins, DNA, and small mols. It is of specific concern as a toxic intermediate in the design of engineered pathways involving methanol oxidation or formate reduction The interest in engineering these pathways is not, however, matched by engineering-relevant information on precisely why HCHO is toxic or on what damage-control mechanisms cells deploy to manage HCHO toxicity. The only well-defined mechanism for managing HCHO toxicity is formaldehyde dehydrogenase-mediated oxidation to formate, which is counterproductive if HCHO is a desired pathway intermediate. We therefore sought alternative HCHO damage-control mechanisms via comparative genomic anal. This anal. associated homologs of the Escherichia coli pepP gene with HCHO-related one-carbon metabolism Furthermore, deleting pepP increased the sensitivity of E. coli to supplied HCHO but not other carbonyl compounds PepP is a proline aminopeptidase that cleaves peptides of the general formula X-Pro-Y, yielding X + Pro-Y. HCHO is known to react spontaneously with cysteine to form the close proline analog thioproline (thiazolidine-4-carboxylate), which is incorporated into proteins and hence into proteolytic peptides. We therefore hypothesized that certain thioproline-containing peptides are toxic and that PepP cleaves these aberrant peptides. Supporting this hypothesis, PepP cleaved the model peptide Ala-thioproline-Ala as efficiently as Ala-Pro-Ala in vitro and in vivo, and deleting pepP increased sensitivity to supplied thioproline. Our data thus (i) provide biochem. genetic evidence that thioproline formation contributes substantially to HCHO toxicity and (ii) make PepP a candidate damage-control enzyme for engineered pathways having HCHO as an intermediate. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Synthetic Route of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Synthetic Route of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Design and synthesis of new substituted spirooxindoles as potential inhibitors of the MDM2-p53 interaction was written by Barakat, Assem;Islam, Mohammad Shahidul;Ghawas, Hussien Mansur;Al-Majid, Abdullah Mohammed;El-Senduny, Fardous F.;Badria, Farid A.;Elshaier, Yaseen A. M. M.;Ghabbour, Hazem A.. And the article was included in Bioorganic Chemistry in 2019.Formula: C4H7NO2S This article mentions the following:

The designed compounds, 4a-p, were synthesized using a simple and smooth method with an asym. 1,3-dipolar reaction as the key step. The chem. structures for all synthesized compounds were elucidated and confirmed by spectral anal. The mol. complexity and the absolute stereochem. of 4b and 4e designed analogs were determined by X-ray crystallog. anal. The anticancer activities of the synthesized compounds were tested against colon (HCT-116), prostate (PC-3), and hepatocellular (HepG-2) cancer cell lines. Mol. modeling revealed that the compound 4d binds through hydrophobic-hydrophobic interactions with the essential amino acids (LEU: 57, GLY: 58, ILE: 61, and HIS: 96) in the p53-binding cleft, as a standard p53-MDM2 inhibitor (6SJ). The mechanism underlying the anticancer activity of compound 4d was further evaluated, and the study showed that compound 4d inhibited colony formation, cell migration, arrested cancer cell growth at G2/M, and induced apoptosis through intrinsic and extrinsic pathways. Transactivation of p53 was confirmed by flow cytometry, where compound 4d increased the level of activated p53 and induced mRNA levels of cell cycle inhibitor, p21. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Formula: C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Formula: C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Ethyl 6′-cyano-7′-phenyl-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole-6′-carboxylate was written by Muthuselvi, C.;Athimoolam, S.;Srinivasan, N.;Ravikumar, B.;Pandiarajan, S.;Krishnakumar, R. V.. And the article was included in IUCrData in 2018.Formula: C4H7NO2S This article mentions the following:

In the title compound, C22H22ClN4O2S, the angle between the mean planes of the indene ring and the quinoxaline ring system is 3.93 (11)°. The five-membered indene and thiazole rings both adopt envelope conformations while the pyrrole ring adopts a twisted conformation. The two acceptor O atoms form a chelated three-centered hydrogen bond with a Ph C atom. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Formula: C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Formula: C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Ambruticins: Tetrahydropyran ring formation and total synthesis was written by Bowen, James I.;Wang, Luoyi;Crump, Matthew P.;Willis, Christine L.. And the article was included in Organic & Biomolecular Chemistry in 2021.Application of 76186-04-4 This article mentions the following:

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formed via the AmbJ catalyzed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclization to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J (I) is described as well as model studies involving epoxidation and cyclizations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were united via a Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alc. gave, after hydrolysis of the lactone, ambruticin J. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Application of 76186-04-4).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. In the thiazolidine nucleus, a large number of substitutions are possible on 2, 4 and 5 positions responsible for enhancing the compound’s pharmaceutical importance. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.Application of 76186-04-4

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides was written by Chen, Liang;Sun, Jing;Xie, Ju;Yan, Chao-Guo. And the article was included in Organic & Biomolecular Chemistry in 2016.Computed Properties of C4H7NO2S This article mentions the following:

The one-pot three-component reaction of secondary α-amino acids, including proline, thiazolidine-4-carboxylic acid, piperidine-2-carboxylic acid and sarcosine with dialkyl acetylenedicarboxylate and N-substituted maleimides in refluxing ethanol afforded functionalized pyrrolo[3,4-a]pyrrolizines, pyrrolo[3′,4′:3,4]pyrrolo[1,2-c]thiazoles, pyrrolo[3,4-a]indolizines and octahydropyrrolo[3,4-c]pyrroles in good yields and with high diastereoselectivity. On the other hand, the similar three-component reaction containing primary α-amino acids, such as glycine, alanine, phenylalanine and leucine, with N-substituted maleimides and two mols. of dialkyl acetylenedicarboxylate gave the corresponding (hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)maleates. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Computed Properties of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. Thiazolidine-2,4-dione (TZD) is an important derivative of thiazolidine with a sulfur and nitrogen atom in positions 1 and 3, and carbonyl in position 4 of the ring. These derivatives have a wide range of medicinal applications such as antiviral, antimicrobial, anticonvulsant, antiinflammatory, and antimalarial activities.Computed Properties of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

A highly stereoselective reaction in aminolysis of 3-acyl-4(S)-isopropyl-1,3-thiazolidinethione with racemic amines was written by Jeong, Tae Myoung;Park, Ki Hun. And the article was included in Taehan Hwahakhoe Chi in 1988.COA of Formula: C6H11NS2 This article mentions the following:

Chiral recognition was observed in aminolysis of title thiazolidinethiones I [R = Me(CH₂)₁₀, 1-C₁₀H₇] by racemic amino acid esters to give an optically active amide (S-excess) and amino acid esters (R-excess). The rate of this aminolysis is affected by steric surrounding; completion of reaction can be easily judged by the disappearance of the original yellow color of I. I were synthesized from (S)-4-isopropyl-1,3-thiazolidine-2-thione and carboxylic acids. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4COA of Formula: C6H11NS2).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine is a heterocyclic compound with five-membered saturated ring with a thioether group and an amine group in 1 and 3 positions of the ring. Open-chain compounds are obtained when thiazolidines are treated with tris(trimethylsilyl)silane in a reaction in which the thiazolidine derivatives act as a source of α-aminoalkyl radicals.COA of Formula: C6H11NS2

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com